CN116836754B - Method for removing heterocyclic amine from sesame oil - Google Patents
Method for removing heterocyclic amine from sesame oil Download PDFInfo
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- CN116836754B CN116836754B CN202310617182.6A CN202310617182A CN116836754B CN 116836754 B CN116836754 B CN 116836754B CN 202310617182 A CN202310617182 A CN 202310617182A CN 116836754 B CN116836754 B CN 116836754B
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- sesame oil
- heterocyclic amine
- quaternary ammonium
- ammonium salt
- oil
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- 235000011803 sesame oil Nutrition 0.000 title claims abstract description 80
- 239000008159 sesame oil Substances 0.000 title claims abstract description 80
- -1 heterocyclic amine Chemical class 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 26
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 19
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 19
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical group [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 19
- 229960003178 choline chloride Drugs 0.000 claims abstract description 19
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 16
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims abstract description 16
- 229960003237 betaine Drugs 0.000 claims abstract description 16
- 238000001179 sorption measurement Methods 0.000 claims abstract description 14
- PSFDQSOCUJVVGF-UHFFFAOYSA-N Harman Natural products C12=CC=CC=C2NC2=C1C=CN=C2C PSFDQSOCUJVVGF-UHFFFAOYSA-N 0.000 claims description 22
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- PSFDQSOCUJVVGF-NSFXFQGJSA-N 1-methyl-9h-pyrido[3,4-b]indole Chemical group C12=CC=CC=C2NC2=C1[13CH]=[13CH][15N]=C2C PSFDQSOCUJVVGF-NSFXFQGJSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 235000013373 food additive Nutrition 0.000 abstract description 3
- 239000002778 food additive Substances 0.000 abstract description 3
- 235000012041 food component Nutrition 0.000 abstract description 3
- 239000005417 food ingredient Substances 0.000 abstract description 3
- 239000003205 fragrance Substances 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 235000013305 food Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000008157 edible vegetable oil Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000207961 Sesamum Species 0.000 description 3
- 235000003434 Sesamum indicum Nutrition 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 150000002830 nitrogen compounds Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000009210 therapy by ultrasound Methods 0.000 description 3
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RWMZLUCRSBRPTG-UHFFFAOYSA-N 2-[amino(methyl)azaniumyl]acetate Chemical compound CN(N)CC(O)=O RWMZLUCRSBRPTG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- VCAQPYXOWLIOSF-UHFFFAOYSA-N acetic acid;sulfuric acid;hydrate Chemical compound O.CC(O)=O.OS(O)(=O)=O VCAQPYXOWLIOSF-UHFFFAOYSA-N 0.000 description 1
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
- 239000002115 aflatoxin B1 Substances 0.000 description 1
- 229930020125 aflatoxin-B1 Natural products 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention relates to a method for removing heterocyclic amine in sesame oil, which comprises the steps of carrying out mixed adsorption on sesame oil by using quaternary ammonium salt, and then separating out the sesame oil from which the heterocyclic amine is removed; the quaternary ammonium salt is choline chloride or betaine. The quaternary ammonium salt used in the invention is green and nontoxic choline chloride and betaine, which can be used as food additives and food ingredients, and is safe and nontoxic; the efficiency of removing heterocyclic amine in sesame oil is high and can reach 97%, the quality of the sesame oil is not affected, and the loss of the fragrance of the sesame oil is not caused. Meanwhile, no new harmful residues are introduced to cause secondary pollution in sesame oil, the method is simple to operate, short in reaction time, safe, effective, economical, environment-friendly and suitable for large-scale popularization and use.
Description
Technical Field
The invention relates to a method for removing heterocyclic amine in sesame oil, belonging to the technical field of processing methods of edible oil sesame oil.
Background
Sesame oil contains abundant unsaturated fatty acids (about 80%), mainly oleic acid and linoleic acid, and also contains lignanoid compounds, fat-soluble vitamins and other nutrients, and has effects of reducing blood lipid, resisting aging, protecting liver, resisting cancer, etc. The sesame roasting process is a key step in the sesame oil production process. The sesame seeds are roasted at high temperature to cause complex chemical reactions of foods, and the components such as proteins/amino acids contained in the sesame seeds are subjected to a series of chemical reactions of foods to generate heterocyclic amines in the process of roasting seeds at high temperature while forming the unique flavor of the sesame oil. In order to retain the peculiar flavor produced by baking, sesame oil is generally obtained by precipitation, cold filtration and the like. Therefore, heterocyclic amine substances entering the finished sesame oil cannot be effectively removed, and the safety risk of the sesame oil is increased. Furthermore, heterocyclic amines in sesame oil are mainly two heterocyclic amine substances of harman and norrhaman, because harman and norrhaman belong to fat-soluble heterocyclic amines and the content of heterocyclic amines in sesame oil is higher than other vegetable oils.
Heterocyclic amine is a polycyclic aromatic compound containing nitrogen heterocycle, is produced by the reaction of free amino, sarcosine, creatinine and saccharides in food under the condition of high temperature, and has stronger carcinogenesis, mutation and myocardial toxicity. Studies have shown that the mutagenicity of heterocyclic amines is one hundred times that of aflatoxin B1 and two thousand times that of benzopyrene, respectively. Therefore, even though the heterocyclic amine is contained in a small amount in the food, it brings about a non-negligible risk of food safety. The European Union has once proposed safety warnings that require the daily intake of heterocyclic amines in foods to be no more than 1mg. Therefore, removal of heterocyclic amines from sesame oil is important.
At present, nitrogen-containing compounds in oil products (oil for chemical industry) are mainly adsorbed, separated and denitrified and extracted. The solid adsorbent commonly used for adsorption separation denitrification comprises silica gel, carbon materials (such as active carbon), metal oxides, zeolite materials and the like, and if the solid adsorbent is applied to stir-fried edible oil (such as sesame oil), the flavor of the oil is not good. Up to now, an adsorption material which has high adsorption performance, high selectivity, low cost and easy use and is environment-friendly has yet to be discovered.
The Chinese patent publication No. CN106631967A discloses a method for extracting and separating indole from wash oil by using a quaternary ammonium salt extractant, wherein quaternary ammonium salt tetramethyl ammonium chloride, tetraethyl ammonium chloride and tetrabutyl ammonium chloride are adopted for extracting and removing nitrogenous compound indole from the wash oil, but the three quaternary ammonium salts have toxicity, and have potential safety hazards when being applied to removing heterocyclic amine nitrogenous compounds from edible oil.
The Chinese patent publication No. CN1088606A discloses a denitrification method for liquid petroleum products, which adopts an extractant composed of low carbon alcohol and water or low carbon alcohol and dilute alkali water solution to extract and remove total nitrogen, basic nitrogen, mercaptan sulfur and low molecular organic acid in the liquid petroleum products, wherein the removal rate of the total nitrogen and the basic nitrogen can reach 50-80 percent.
The Chinese patent of invention with the authority of CN104762100B discloses a method for extracting and removing nitrogen-containing compounds in oil products by using a eutectic solvent as an extracting agent, wherein the eutectic solvent is required to be composed of a hydrogen bond acceptor compound A (choline chloride, betaine and amino acid) and a hydrogen bond acceptor compound B (such as dicarboxylic acid and urea), and the removal rate of the nitrogen-containing compounds in the oil products by extraction is more than 80 percent.
The U.S. patent No. 4790930 adopts carboxylic acid aqueous solution with mass fraction of 20% -95% to extract nitrogenous heterocyclic compounds from decompressed wax oil and coker diesel, and the denitrification rate is 26% -63%.
Russian patent RU2257398 uses a sulfuric acid-acetic acid-water mixture to extract and remove nitrogen compounds from oil products. Generally, the acid extraction method has better removal effect on basic nitrogen compounds, but generally has the problems of low removal rate of non-basic nitrogen compounds, low oil yield, corrosion to equipment, large environmental pollution, difficult treatment of acid residues and the like.
The US patent US5494572 uses a nitrogen-containing heterocyclic solvent such as pyrrolidone, an amide solvent, or a mixture of a pyridine salt and water or a liquid lower alcohol as an extractant to remove nitrogen-containing compounds in light oil, and found that the denitrification rate gradually increases to 90% or more with increasing extractant usage, but the oil yield gradually decreases to 61% or less. Because of a certain mutual solubility of the organic solvent and the oil, the organic solvent extraction denitrification technology generally has the problems of low oil yield, easy secondary pollution of the denitrified oil by the organic solvent and the like, and the removal effect on basic nitrogen is not ideal.
The method can remove nitrogen-containing substances in the oil, but is difficult to apply to effectively removing heterocyclic amine substances in the edible oil, and has relatively complex operation, longer time and relatively lower removal efficiency.
Disclosure of Invention
The invention aims to provide a method for removing heterocyclic amine in sesame oil, which can effectively improve the removal effect of heterocyclic amine in sesame oil, is simple to operate and does not affect the quality and flavor of the sesame oil; meanwhile, no new harmful residues are introduced, and the method is environment-friendly.
In order to achieve the above purpose, the technical scheme of the method for removing heterocyclic amine in sesame oil in the invention is as follows:
a method for removing heterocyclic amine in sesame oil comprises the steps of carrying out mixed adsorption on sesame oil by using quaternary ammonium salt, and then separating out the sesame oil from which the heterocyclic amine is removed; the quaternary ammonium salt is choline chloride or betaine.
The beneficial effects of the technical scheme are that: according to the invention, the quaternary ammonium salt is mixed with the sesame oil, the heterocyclic amine in the sesame oil is combined with the quaternary ammonium salt or the quaternary ammonium salt aqueous solution through hydrogen bond, and then the subsequent separation operation is carried out, so that the effective removal of the heterocyclic amine in the sesame oil is realized, and the removal rate of the heterocyclic amine can reach more than 86%.
As a further improvement, the mass ratio of the quaternary ammonium salt to the sesame oil is 0.1-1.0. Preferably, the mass ratio of the quaternary ammonium salt to the sesame oil is 0.3-0.5.
The beneficial effects of the technical scheme are that: when the mass ratio of the quaternary ammonium salt to the sesame oil is 0.1-1.0, the effective removal of heterocyclic amine in the sesame oil can be realized, and the dosage is small.
As a further improvement, the quaternary ammonium salt is mixed and adsorbed with sesame oil in the form of a solution; each 1mL of the solution contains 0.5-1.0g of quaternary ammonium salt. Preferably, 0.6-0.9g quaternary ammonium salt is contained per 1mL of the solution.
The beneficial effects of the technical scheme are that: experiments prove that the removal rate of the heterocyclic amine in the sesame oil can reach 97.3% by using the quaternary ammonium salt solution to adsorb the heterocyclic amine.
As a further improvement, after the mixed adsorption, sesame oil from which heterocyclic amine is removed is obtained by liquid separation.
Specifically, the mixed adsorption may be carried out by ultrasonic treatment or stirring treatment.
As a further improvement, the temperature of the mixed adsorption is 10-80 ℃.
As a further improvement, the temperature of the mixed adsorption is 40-60 ℃.
The beneficial effects of the technical scheme are that: the extraction temperature is too low, the viscosity of grease is larger, the mass transfer rate between two phases (sesame oil and quaternary ammonium salt) is reduced, the time required for reaching the extraction balance is longer, and the production operation is not facilitated; the extraction temperature is properly increased, the viscosity of grease is reduced, and the mass transfer rate is increased; the extraction temperature is too high, so that the production energy consumption is increased, and grease oxidation can be caused. The temperature of the mixed adsorption is 10-80 ℃, preferably 40-60 ℃, so that the heterocyclic amine in the sesame oil can be effectively removed, and the production cost is reduced.
As a further improvement, the heterocyclic amine is 1-methyl-9H-pyrido [3,4-b ] indole (1-methyl-9H-pyrido [3,4-b ] indole, harman) and/or 9H-pyrido [3,4-b ] indole (9H-pyrido [3,4-b ] indole, norrhaman).
The beneficial effects of the technical scheme are that: the heterocyclic amine in sesame oil is mainly two heterocyclic amine substances, namely harman and nonrhaman, and the removal of the heterocyclic amine can further improve the food safety of the sesame oil.
Compared with the prior art, the invention has the beneficial effects that:
1. the quaternary ammonium salt used in the invention is green and nontoxic choline chloride and betaine, which can be used as food additives (food ingredients), is safe and nontoxic, has no influence on the quality of sesame oil, and can not cause the loss of the fragrance of the sesame oil.
2. The method of the invention can not introduce new harmful residues to cause secondary pollution in sesame oil, has high efficiency of removing heterocyclic amine which can reach more than 95 percent, is simple to operate, has short treatment time, is safe, effective, economical and environment-friendly, and is easy to popularize and use on a large scale.
Detailed Description
The present invention will be further described with reference to the following specific embodiments, and it should be noted that, on the premise of no conflict, new embodiments may be formed by any combination of the embodiments or technical features described below. The equipment and materials used, etc., are commercially available or are conventional in the art. The methods in the following examples are conventional in the art unless otherwise specified.
1. Specific example of method for removing heterocyclic amine from sesame oil
Example 1
The method for removing heterocyclic amine in sesame oil in this embodiment is specifically implemented as follows:
50g of sesame oil (sesame oil) was placed in a beaker, to which 25g of choline chloride was added, followed by ultrasonic treatment at 55℃under heating for 5 minutes (ultrasonic power: 390 w). And then removing choline chloride solid by adopting centrifugal separation to obtain sesame oil with heterocyclic amine removed.
Example 2
The method for removing heterocyclic amine in sesame oil in this embodiment is specifically implemented as follows:
50g of sesame oil (sesame oil) was placed in a round-bottomed flask, 25mL of choline chloride/water solution (1 mL of choline chloride/water solution containing 0.87g of choline chloride) was added thereto, and then stirring treatment was performed under heating at 40℃for 40 minutes (rotation speed 1300 rpm). And then separating to remove the choline chloride/water solution, thereby obtaining the sesame oil with heterocyclic amine removed.
Example 3
The method for removing heterocyclic amine in sesame oil in this embodiment is specifically implemented as follows:
50g of sesame oil (sesame oil) was placed in a beaker, 25g of betaine was added thereto, and then ultrasonic treatment was performed under heating at 55℃for 5 minutes (ultrasonic power: 390 w). And then removing betaine solid by adopting centrifugal separation to obtain sesame oil with heterocyclic amine removed.
Example 4
The method for removing heterocyclic amine in sesame oil in this embodiment is specifically implemented as follows:
50g of sesame oil (sesame oil) was placed in a round-bottomed flask, 25mL of an aqueous betaine solution (1 mL of betaine/aqueous solution containing 0.68g of betaine) was added thereto, and then stirring treatment was performed at 40℃under heating for 40 minutes (rotation speed 1300 rpm). And then separating to remove betaine/water solution, thus obtaining sesame oil with heterocyclic amine removed.
2. Comparative example
Comparative example 1
The method for removing heterocyclic amine in sesame oil of this comparative example is different from example 1 in that: the choline chloride was replaced with an equal amount of tetramethylammonium chloride.
Comparative example 2
The method for removing heterocyclic amine in sesame oil of this comparative example is different from example 1 in that: the choline chloride was replaced with an equal amount of triethylmethyl ammonium chloride.
Comparative example 3
The method for removing heterocyclic amine in sesame oil of this comparative example is different from example 1 in that: the choline chloride was replaced with an equivalent amount of ammonium chloride.
3. Experimental example
In this experimental example, the amounts of heterocyclic amine norrhaman and heterocyclic amine harman in sesame oil before and after removal in examples 1 to 4 and comparative examples 1 to 3 were measured, and the removal rates of heterocyclic amine norrhaman and heterocyclic amine harman were calculated.
Extracting heterocyclic amine in sesame oil by acetonitrile, purifying by using a cation solid phase extraction column, and performing liquid chromatography-tandem mass spectrometry analysis. The removal rates of the heterocyclic amine norrhaman, the heterocyclic amine harman and the total heterocyclic amine removal rates in examples 1 to 4 and comparative examples 1 to 3 are shown in Table 1.
Table 1 removal rate of heterocyclic amine from sesame oil in examples and comparative examples
According to the experimental results of table 1, the removal rates of the heterocyclic amines norrhaman and harman in sesame oil by choline chloride and betaine were higher than those of tetramethyl ammonium chloride, triethyl methyl ammonium chloride and ammonium chloride, and the removal rates of the heterocyclic amines norrhaman and harman in sesame oil were higher than those of the solid forms using choline chloride and betaine when aqueous solutions of choline chloride and betaine were used. In addition, choline chloride and betaine can be used as food additives and food ingredients, and are environment-friendly quaternary ammonium salts with rich sources and no toxicity.
The present invention is not limited to the preferred embodiments, and the patent protection scope of the invention is defined by the claims, and all equivalent structural changes made by the application of the present invention are included in the scope of the invention.
Claims (5)
1. A method for removing heterocyclic amine from sesame oil, which is characterized by comprising the following steps: mixing and adsorbing sesame oil by using quaternary ammonium salt, and separating out sesame oil from which heterocyclic amine is removed; the quaternary ammonium salt is choline chloride or betaine; the mass ratio of the quaternary ammonium salt to the sesame oil is 0.1-1.0; the temperature of the mixed adsorption is 10-80 ℃.
2. The method for removing heterocyclic amine from sesame oil according to claim 1, wherein: the quaternary ammonium salt is mixed with sesame oil in the form of solution for adsorption; each 1mL of the solution contains 0.5-1.0g of quaternary ammonium salt.
3. The method for removing heterocyclic amine from sesame oil according to claim 2, wherein: after the mixed adsorption, separating liquid to obtain sesame oil with heterocyclic amine removed.
4. The method for removing heterocyclic amine from sesame oil according to claim 1, wherein: the temperature of the mixed adsorption is 40-60 ℃.
5. The method for removing heterocyclic amine from sesame oil according to claim 1, wherein: the heterocyclic amine is 1-methyl-9H-pyrido [3,4-b ] indole and/or 9H-pyrido [3,4-b ] indole.
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Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103038195A (en) * | 2010-06-22 | 2013-04-10 | 乌尔里希·迪茨 | Device and method for solubilizing, separating, removing and reacting carboxylic acids in oils, fats, aqueous or organic solutions by means of micro- or nanoemulsification |
| CN104762100A (en) * | 2015-03-30 | 2015-07-08 | 浙江大学 | Method for removing nitrogen-containing compounds in oil products by virtue of eutectic solvent extraction |
| CN106236606A (en) * | 2015-06-05 | 2016-12-21 | 国际香料和香精公司 | Stench offsets compositions |
| CN108211423A (en) * | 2018-02-28 | 2018-06-29 | 北京化工大学 | It is a kind of by the use of biodegradable compound as the method for phenolic compound in adsorbent adsorbing separation oil |
| CN108531284A (en) * | 2018-03-15 | 2018-09-14 | 河南亨通粮油食品有限公司 | A kind of production method of high-quality sesame oil |
| CN108887409A (en) * | 2018-09-19 | 2018-11-27 | 铜陵大通小磨麻油有限公司 | A kind of Health-care sesame oil and preparation method thereof |
| CN109022126A (en) * | 2018-07-26 | 2018-12-18 | 望江县振兴植物油厂（普通合伙） | A kind of preparation method of high-quality sesame oil |
| CN109652209A (en) * | 2018-11-15 | 2019-04-19 | 杭州女舒生物科技有限公司 | The quantitative analysis method of the extracting method and its active component of rose ethereal oil |
| CN109704919A (en) * | 2018-12-28 | 2019-05-03 | 浙江工业大学 | Water-methanol based on choline chloride eutectic solvent-alcohol mixture extraction and rectification separation method |
| CN110079387A (en) * | 2019-05-28 | 2019-08-02 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of method that the extraction of ultrasonic wave added eutectic solvent removes cholesterol in lard |
| CN113186024A (en) * | 2021-04-13 | 2021-07-30 | 华南理工大学 | Strong-flavor peanut oil based on eutectic solvent and preparation method thereof |
| CN115216330A (en) * | 2022-07-11 | 2022-10-21 | 青岛科技大学 | Method for separating nitrogen-containing compounds in oil products |
| CN116144420A (en) * | 2023-04-20 | 2023-05-23 | 山东丰香园食品股份有限公司 | Production process of cold-pressed sesame oil |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112779096A (en) * | 2021-01-11 | 2021-05-11 | 上海应用技术大学 | Method for extracting plant essential oil by using double auxiliary agents |
-
2023
- 2023-05-29 CN CN202310617182.6A patent/CN116836754B/en active Active
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103038195A (en) * | 2010-06-22 | 2013-04-10 | 乌尔里希·迪茨 | Device and method for solubilizing, separating, removing and reacting carboxylic acids in oils, fats, aqueous or organic solutions by means of micro- or nanoemulsification |
| CN104762100A (en) * | 2015-03-30 | 2015-07-08 | 浙江大学 | Method for removing nitrogen-containing compounds in oil products by virtue of eutectic solvent extraction |
| CN106236606A (en) * | 2015-06-05 | 2016-12-21 | 国际香料和香精公司 | Stench offsets compositions |
| CN108211423A (en) * | 2018-02-28 | 2018-06-29 | 北京化工大学 | It is a kind of by the use of biodegradable compound as the method for phenolic compound in adsorbent adsorbing separation oil |
| CN108531284A (en) * | 2018-03-15 | 2018-09-14 | 河南亨通粮油食品有限公司 | A kind of production method of high-quality sesame oil |
| CN109022126A (en) * | 2018-07-26 | 2018-12-18 | 望江县振兴植物油厂（普通合伙） | A kind of preparation method of high-quality sesame oil |
| CN108887409A (en) * | 2018-09-19 | 2018-11-27 | 铜陵大通小磨麻油有限公司 | A kind of Health-care sesame oil and preparation method thereof |
| CN109652209A (en) * | 2018-11-15 | 2019-04-19 | 杭州女舒生物科技有限公司 | The quantitative analysis method of the extracting method and its active component of rose ethereal oil |
| CN109704919A (en) * | 2018-12-28 | 2019-05-03 | 浙江工业大学 | Water-methanol based on choline chloride eutectic solvent-alcohol mixture extraction and rectification separation method |
| CN110079387A (en) * | 2019-05-28 | 2019-08-02 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of method that the extraction of ultrasonic wave added eutectic solvent removes cholesterol in lard |
| CN113186024A (en) * | 2021-04-13 | 2021-07-30 | 华南理工大学 | Strong-flavor peanut oil based on eutectic solvent and preparation method thereof |
| CN115216330A (en) * | 2022-07-11 | 2022-10-21 | 青岛科技大学 | Method for separating nitrogen-containing compounds in oil products |
| CN116144420A (en) * | 2023-04-20 | 2023-05-23 | 山东丰香园食品股份有限公司 | Production process of cold-pressed sesame oil |
Non-Patent Citations (4)
| Title |
|---|
| 低共熔溶剂对煤焦油柴油馏分中氮化物的脱除;赵宁;刘东;李志恒;郭中山;娄斌;于冉;王峰;;石油学报(石油加工);20200325(第02期);第410-419页 * |
| 基于低共熔溶剂的液相微萃取-高效液相色谱法测定大豆油中的TBHQ;张康迪等;河南工业大学学报(自然科学版);20171031;第38卷(第05期);第32-36页 * |
| 菜籽油低共熔溶剂萃取物DPPH自由基清除能力研究;毛立忠;倪勤学;高前欣;许光治;张有做;;中国粮油学报;20180203(第02期);第50-55页 * |
| 高蛋白食品中杂环胺形成与控制的研究进展;席俊等;河南工业大学学报(自然科学版);20210430;第42卷(第02期);第112-120页 * |
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